Synthesis and Crystallographic Characterization of 1-((2-(2,4-Difluorophenyl)oxiran-2-yl)methyl)-1<Emphasis Type="Italic">H</Emphasis>-1,2,4-triazole: A Crucial Intermediate for the Synthesis of Azole Antifungal Drugs |
| |
| Authors: | Pallav D Patel Tanaji T Talele Frank R Fronczek |
| |
| Institution: | (1) Department of Pharmaceutical Sciences, College of Pharmacy and Allied Health Professions, St. John’s University, Jamaica, NY 11439, USA;(2) Department of Chemistry, Louisiana State University, Baton Rouge, LA 70803, USA; |
| |
| Abstract: | Abstract Preparation of oxirane 3 was accomplished in two steps. 1H-1,2,4-triazole was reacted with 2,4-difluoro-α-chloroacetophenone 1 in presence of K2CO3 in refluxing toluene to provide compound 2. Compound 2 was treated with trimethylsulfoxonium iodide (TMSI) in aq. NaOH and toluene to provide oxirane 3. Oxirane 3, previously isolated as an oil, was crystallized from (DCM/MeOH) and characterized by X-ray crystallography: triclinic, space group P − 1, a = 7.3225 (15), b = 7.5833 (15), c = 9.856 (2) Å, α = 91.908 (12), β = 100.824 (11), γ = 103.800 (11)°, V = 520.28 (18) Å3, Z = 2. The molecule has a stepped conformation with nearly parallel triazole and phenyl rings. Lack of classical hydrogen-bond
donors leads to packing dominated by weaker interactions, including C–H···N, C–H···F and F···F contacts. |
| |
| Keywords: | |
| 本文献已被 SpringerLink 等数据库收录！ |
|
